Facile synthesis of aromatic unsymmetrical fluorine-containing acyloins through the reductive trifluoroacetylation of benzaldehyde and transposition of the carbonyl group

Maekawa, Hirofumi; Kudo, Masashi; Nishiyama, Yutaro; Shimizu, Kazuyuki; Abe, Mitsuhiro

doi:10.1016/j.tet.2014.02.016

Cited by 11 publications

(3 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Certain progress has been made in the synthesis of trifluoromethyl aromatic acyloins. Maekawa's group [24] developed a tandem reaction of the reductive coupling between arylalde-Scheme 1: Strategies for the synthesis of α-trifluoromethyl acyloins. hydes and ethyl trifluoroacetate in the presence of magnesium and chlorotrimethylsilane, followed by desilylation to produce the trifluoromethyl aromatic acyloins (Scheme 1a).…”

Section: Introductionmentioning

confidence: 99%

“…Certain progress has been made in the synthesis of trifluoromethyl aromatic acyloins. Maekawa’s group [ 24 ] developed a tandem reaction of the reductive coupling between arylaldehydes and ethyl trifluoroacetate in the presence of magnesium and chlorotrimethylsilane, followed by desilylation to produce the trifluoromethyl aromatic acyloins ( Scheme 1a ). Anand’s group [ 25 ] demonstrated that a NHC-catalyzed selective acyloin condensation between aromatic aldehydes and trifluoroacetaldehyde ethyl hemiacetal afforded the analogous products ( Scheme 1b ).…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Visible-light-induced nickel-catalyzed α-hydroxytrifluoroethylation of alkyl carboxylic acids: Access to trifluoromethyl alkyl acyloins

Chen,

Xu,

Chen

et al. 2023

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

A visible-light-induced nickel-catalyzed cross coupling of alkyl carboxylic acids with N-trifluoroethoxyphthalimide is described. Under purple light irradiation, an α-hydroxytrifluoroethyl radical generated from a photoactive electron donor–acceptor complex between Hantzsch ester and N-trifluoroethoxyphthalimide was subsequently engaged in a nickel-catalyzed coupling reaction with in situ-activated alkyl carboxylic acids. This convenient protocol does not require photocatalysts and metal reductants, providing a straightforward and efficient access to trifluoromethyl alkyl acyloins in good yields with broad substrate compatibility. The complex bioactive molecules were also compatible with this catalytic system to afford the corresponding products.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Visible-light-induced nickel-catalyzed α-hydroxytrifluoroethylation of alkyl carboxylic acids: Access to trifluoromethyl alkyl acyloins

Chen,

Xu,

Chen

et al. 2023

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…An important milestone for the synthesis of fluorine-containing furan derivatives is the preparation of trifluoromethylated furans through a coupling reaction between enones and trifluoroacetic anhydride as reported by Xu and co-workers in 2011 (Scheme , b) . We also disclosed synthetic reactions of partially fluorinated compounds by magnesium-promoted reduction . For instance, trifluoroacetylation of 4-vinylpyridines in the presence of ethyl trifluoroacetate afforded the corresponding β-monotrifluoroacetylated compounds in good yields…”

mentioning

confidence: 99%

Synthesis of 4-(Trifluoromethyl)cyclopentenones and 2-(Trifluoromethyl)furans by Reductive Trifluoroacetylation of Ynones

Zhang

Maekawa

2017

Org. Lett.

Self Cite

View full text Add to dashboard Cite

Reductive introduction of a fluorine-containing carbon block to readily available conjugated ynones, followed by intramolecular cyclization, successfully gave the corresponding trifluoromethylated cyclopentenones or trifluoromethylated furans in good yields through a simple two-step protocol. The key compound in carbon-carbon bond formation by magnesium-promoted reduction is ethyl trifluoroacetate, which has been rarely used as a fluorine-containing carbon source, especially to electron-deficient carbon atoms in organic synthesis.

show abstract

Selective Introduction of Trifluoroacetyl Group to β‐ and δ‐Position of Aromatic Conjugated Esters: Facile Synthesis of Fluorine‐containing Keto Esters

Zhang

Shimizu

et al. 2019

Asian J Org Chem

Self Cite

View full text Add to dashboard Cite

An approach to trifluoroacetylation of aromatic conjugated esters successfully led to the efficient and selective introduction of trifluoroacetyl group to the electron-deficient βor δ-carbon atom of ester under mild reaction conditions by magnesium-promoted reduction, followed by deacetalization with trifluoroacetic acid in moderate to good yields. A variety of fluorinated keto esters derived from ethyl cinnamates and β, γor γ-, δunsaturated fluorinated keto esters from aromatic dienoesters with a longer conjugation system were synthesized through this simple methodology utilizing ethyl trifluoroacetate as a fluorine-containing carbon source.

show abstract

Facile synthesis of aromatic unsymmetrical fluorine-containing acyloins through the reductive trifluoroacetylation of benzaldehyde and transposition of the carbonyl group

Cited by 11 publications

References 26 publications

Visible-light-induced nickel-catalyzed α-hydroxytrifluoroethylation of alkyl carboxylic acids: Access to trifluoromethyl alkyl acyloins

Visible-light-induced nickel-catalyzed α-hydroxytrifluoroethylation of alkyl carboxylic acids: Access to trifluoromethyl alkyl acyloins

Synthesis of 4-(Trifluoromethyl)cyclopentenones and 2-(Trifluoromethyl)furans by Reductive Trifluoroacetylation of Ynones

Selective Introduction of Trifluoroacetyl Group to β‐ and δ‐Position of Aromatic Conjugated Esters: Facile Synthesis of Fluorine‐containing Keto Esters

Contact Info

Product

Resources

About